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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.8K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.0K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.0K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.0K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Updated: May 30, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Asymmetric Functionalization Harnessing Radical-Mediated Functional-Group Migration.

Fushan Chen1, Zhu Cao1, Chen Zhu1

  • 1Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.

Angewandte Chemie (International Ed. in English)
|January 27, 2025
PubMed
Summary
This summary is machine-generated.

This review covers asymmetric functionalization using radical-mediated functional-group migration (FGM) reactions. These methods enable the creation of complex molecules with high enantioselectivity, overcoming challenges in asymmetric radical chemistry.

Keywords:
asymmetric synthesisfunctional-group migrationradical reactionsrearrangementsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Radical chemistry has seen significant advancements, particularly in radical-mediated rearrangement reactions.
  • Functional-group migration (FGM) reactions have been developed to improve synthetic efficiency and molecular complexity.

Purpose of the Study:

  • To summarize the emerging field of asymmetric functionalization via radical-mediated FGM reactions.
  • To highlight strategies for achieving enantioselectivity in these reactions.

Main Methods:

  • Review of existing literature on asymmetric radical-mediated FGM reactions.
  • Discussion of enantioselectivity control using chiral substrates, auxiliaries, reagents, or asymmetric transition-metal catalysis.

Main Results:

  • Enantioselective synthesis of complex molecules is achievable through radical-mediated FGM.
  • Various strategies exist for controlling enantioselectivity in these reactions.

Conclusions:

  • Asymmetric radical-mediated FGM is a powerful strategy for synthesizing valuable complex molecules.
  • This approach offers advantages over conventional methods for certain synthetic targets.